Disperse and acid azo dyes having one or two cinnamoyl substituents on a phenyl diazonium moiety and containing an aniline, tetrahydroquinoline or benzomorpholine coupler

ABSTRACT

This invention relates to azo dyes which may be unsubstituted or substituted with a variety of groups known to the dye art, and containing a diazonium moieties from an aniline type compound and certain coupler moieties from aniline, tetrahydroquinoline, or benzomorpholine compounds, wherein the diazonium moiety has one or two cinnamoyl substituents, and wherein one or more water-solubilizing groups such as a sulfonic acid group or its metal or amine salt may be present as a substituent in the dye molecule for acid dyeing. These dyes are particularly useful in dyeing one or more of polyamide cellulose acetate polyester, wool and other fibers.

This invention relates to azo dyes containing a diazonium moiety from ananiline type compound, and certain coupler moieties from aniline,tetrahydroquinoline, and benzomorpholine type compounds, wherein thediazonium moiety has one or two cinnamoyl groups, and wherein a widevariety of groups, e.g., one or more water-solubilizing substituentssuch as sulfonic acid groups or their metal or amine salts may bepresent in the dye molecule. These dyes are useful for dyeing materialsselected from polyamide, cellulose ester, polyester, wool and othernatural and synthetic fibers and generally exhibit improvements indyeability and fastness properties.

The present dyes have the general structure: ##STR1## wherein C¹ is ananiline, tetrahydroquinoline, or benzomorpholine type coupler which maybe substituted; ring A is unsubstituted or substituted in any positionsnot occupied by cinnamoyl groups, with 1-3 substituents preferably eachof which is a substituent as defined for R₁ ; R₅ is H or alkyl; and eachR₁ is alkyl, alkenyl of 2-6 carbons, aryl, cyclohexyl, alkoxy, halogen,hydroxy, alkylsulfonyl, cyano, carbamoyl, alkanoyl, alkanoyloxy, aroyl,alkoxycarbonyl, sulfamoyl, alkylsulfamoyl, dialkylsulfamoyl,alkanoylamino, SO₃ C₆ H₅, amino, alkylthio, thiocyano, arylsulfonyl,formyl, alkylcarbamoyl, dialkylcarbamoyl, NO₂, --SO₃ M, --OSO₃ M,--COOH, aryloxy, arylthio, alkylsulfonylamino, aroylamino,arylsulfonylamino, or cyclohexylthio, wherein the alkyl, alkylene,alkenyl, aryl, and cyclohexyl moieties of the above R₁ groups, e.g., thealkyl portions of the alkanoyl groups, are unsubstituted or substitutedwith 1-3 substituents different from the said moieties and independentlyselected from alkanoyloxy, alkyl, alkenyl, succinimido (C₄ H₄ O₂ N),--NO₂, alkanoylamino, alkylsulfonylamino, 1-(2-pyrrolidono) (C₄ H₆ ON),halogen, cyano, alkoxy, aryl, cyclohexyl, hydroxy, --SO₃ M, --OSO₃ M,aryloxy, furyl (C₄ H₃ O), aroyloxy, alkoxycarbonyl, --SO₂ N-(alkyl)₂,--NHCOO-alkyl, --NHCONH-alkyl, glutarimido (C₅ H₆ O₂ N), phthalimido (C₈H₄ O₂ N), CONH₂, CONH-alkyl, CON(alkyl)₂, alkoxyalkoxy, alkylthio,arylthio, alkylsulfonyl, and arylsulfonyl, wherein M is selected fromH⁺, NH₄ ⁺, Na⁺, K⁺, and the colorless cations of salts of primary,secondary, and tertiary aliphatic and arylamines, such as triethylamine,tri(2-hydroxyethyl)amine, di(2-hydroxyethyl)amine, N,N-dimethylaniline,and especially trimethylamine.

The couplers C¹ preferably have the formulae: ##STR2## wherein R₁ isdefined above; R₂ and R₇ are each selected independently from hydrogen,alkyl, alkenyl of 2-6 carbons, aryl, and cyclohexyl, all of which groupsincluding alkylene moieties are unsubstituted or substituted as definedabove for the substituted R₁ groups; and R₃, R₄ and R₈ are each selectedfrom hydrogen and alkyl.

The various alkyl and alkylene moieties such as contained, for example,in alkoxy, alkanoyl, and alkoxyalkoxy groups within the abovedefinitions preferably contain 1-6 carbons, and they and the alkenylgroups may be straight or branched chain, and the above aryl groupspreferably contain from 6-10 ring carbons.

The following are typical specific R₁ groups: CH₃, Cl, SO₂ C₂ H₅, CN,CONH₂, COC₂ H₅, COC₆ H₅, COOC₂ H₅, SO₂ NH₂, SO₂ NHCH₃, SO₂ N(C₂ H₅)₂,NHCOC₂ H₅, SO₃ C₆ H₅, SCH₃, SCN, SO₂ C₆ H₅, CHO, CONHC₂ H₅, CON(C₂ H₅)₂,OH, NO₂, C₆ H₅, C₆ H₁₁, SO₃ K, CF₃, CH₂ OOCC₂ H₅, Br, SO₂ CH₂ CH₂ OC₂H₅, I, CONHCH₂ CN, COCH₂ CH₂ OH, COC₆ H₃ -o-CH₃ -p-OCH₃, COOC₂ H₄-CH═CH₂, SO₂ NHCH₂ CH₂ CN, SO₂ NHCH₂ -succinimido, SO₂ NHC₂ H₄ -C₆ H₅,NHCOCH₂ CH₂ Cl, SO₃ C₆ H₄ -p-NO₂, SCH₂ CH.sub. 2 OH, SC₂ H₄ -C₆ H₁₁, SO₂C₆ H₄ -p-NHCOCH₃, C₆ H₄ -p-NHSO₂ CH₃, CONHC₂ H₄ NHSO₂ CH₃, CONHCH₂ CH₂OH, CH₂ CH₂ NO₂, C₆ H₄ -p-(2-pyrrolidono), C₆ H₁₀ -4-CN, OSO₃ K, CH₂ SO₃Na, OC₆ H₅, SO₂ C₂ H₄ OSO₃ K, C₂ H₄ -furyl, C₂ H₄ OOCC₆ H₅, COCH₂ CH₂COOCH₃, COC₆ H₄ -p-SO₂ NHC₆ H₅, COOCH₂ CH₂ -SO₂ NHCH₃, SO₂ NHCH₂ SO₂N(C₂ H₅)₂, SO₂ NHCH₂ NHCOOCH₃, SO₂ NHC₂ H₄ NHCONHCH₃, NHCOCH₂ CH₂-glutarimido, SO₃ C₆ H₄ -p-phthalimido, SCH₂ CONH₂, C₆ H₄ -p-SO₂ CH₃,SO₂ C₆ H₄ -p-CONHCH₂ SO₃ Na, CH₂ SO₂ C₆ H.sub. 5, CONHCH₂ CH₂ CON(CH₃)₂,CONHCH₂ CH₂ OCH₂ CH₂ OCH₂ CH₃, CH₂ CH₂ SO₃ H, C₆ H₄ -p-SC₂ H₅, C₆ H₁₀-4-SC₆ H₄ (p-OSO₃ H), CH₂ CH═CH₂, COOH, OC₆ H₅, OCH₃, SC₆ H₅, NHSO₂ CH₃,NHCOC₆ H₅, NH₂, NHSO₂ C₆ H₅, SC₆ H₁₁, and --OOCCH₃.

Typical for R₃, R₄, R₅ and R₈ are: H, CH₃, C₂ H₅, C₄ H₉ -n, and CH₂(CH₃)₂.

The following are typical specific R₂ and R₇ substituents: H, CH₃, C₂H₅, C₄ H₉ -n, CH₂ CH═CH₂, C₆ H₅, C₆ H₁₁, CH₂ OOCC₂ H₅, CH₂ CH₂ OC₂ H₅,CH₂ CN, CH₂ CH₂ OH, C₆ H₃ -o-CH₃ -p-OCH₃, C₂ H₄ -CH═CH₂, CH₂-succinimido, CH₂ CH₂ -C₆ H₅, CH₂ CH₂ Cl, C₆ H₄ -p-NO₂, CH₂ CH₂ C₆ H₁₁,C₆ H₄ -p-NHSO₂ CH₃, C₂ H₄ NHSO₂ CH₃, CH₂ CH₂ NO₂, C₆ H₄-p-(2-pyrrolidono), C₆ H₁₀ -4-CN, CH₂ SO₃ Na, CH₂ CH₂ OSO₃ K, CH₂ CH₂-furyl, CH₂ CH₂ OOCC₆ H₅, CH₂ CH₂ COOCH₃, C₆ H₅ -p-SO₂ NHC₆ H₅, CH₂ CH₂SO₂ NHCH₃, CH₂ SO₂ N(C₂ H₅)₂, CH₂ NHCOOCH₃, CH₂ CH₂ NHCONHCH₃, CH₂ CH₂-glutarimido, C₆ H₄ -p-phthalimido, CH₂ CONH₂, C₆ H₄ -p-SO₂ CH₃, C₆ H₄-p-CONHCH₂ SO₃ Na, CH₂ SO₂ C₆ H₅, CH₂ CH₂ CON(CH₃)₂, CH₂ CH₂ OCH₂ CH₂OC₂ H₅, CH₂ CH₂ SO₃ H, C₆ H₄ -p-SC₂ H₅, and C₆ H.sub. 10 -4-SC₆ H₄(p-OSO₃ H).

Preferred substituents, in addition to H, for the A ring are halogen,CN, methoxycarbonyl, alkoxy, CF₃, NO₂, alkanoyl, alkylsulfonyl,β-hydroxyethylcarbamoyl, β-potassiosulfatoethylcarbamoyl,methylcarbamoyl, carbamoyl, ethoxycarbonyl, or methyl; for R₁ on thecinnamoyl rings are H, alkyl, aralkyl, aralkyl substituted with --SO₃ Mor --SO₄ M, cyclohexylalkyl, cyclohexylalkyl substituted with --SO₃ M or--SO₄ M, alkoxy, or alkanoylamino; for R₂ are H, alkyl, aralkyl, alkylor aralkyl substituted with --SO₃ M or --SO₄ M, cyclohexylalkyl,cyclohexylalkyl substituted with --SO₃ M or --SO₄ M; for R₇ are H,alkyl, aralkyl, aralkyl substituted with --SO₃ M or --SO₄ M,cyclohexylalkyl, cyclohexylalkyl substituted with --SO₃ M or --SO₄ M,sodio- or potassiosulfatoalkyl, sodio- or potassiosulfonicalkyl, oralkanoyloxyalkyl; for R₁ on the couplers are H, aralkyl, aralkylsubstituted with --SO₃ M or --SO₄ M, cyclohexylalkyl, cyclohexylalkylsubstituted with --SO₃ M or --SO₄ M, --SO₃ Na, --SO₃ K, halogen, --SO₄Na, --SO₄ K, alkyl, alkoxy, --COOH, or --OH; for R₃, R₄ and R₈ are H andalkyl; and for R₅ is hydrogen.

The dyes of this invention impart red to blue shades on natural andsynthetic fibers and exhibit improvements over such dyes as disclosed inU.S. Pat. No. 2,805,218 and British Pat. No. 1,021,399 in one or moreproperties such as fastness to light, ozone, chlorine, oxides ofnitrogen, washing, sublimation, heat disintegration, perspiration, andcrocking, leveling, transfer, exhaustion, build, pH stability, andresistance to blooming.

The intermediate compounds used in this invention are prepared accordingto procedures well known to the art. The present dyes are readilyprepared, for example, by reacting the acetyl group of the intermediateazo compound, which itself is a dye, with benzaldehyde or a substitutedbenzaldehyde in acetic acid with concentrated sulphuric acid ascatalyst. The acetyl dye is thus converted to a cinnamoyl substituteddye in high yield. The water-solubilizing group may be the substituenton the benzaldehyde or it may be introduced into the cinnamoyl dye at alater stage by known methods. For example, a hydroxy group in either thediazonium component or the coupling component could be reacted withsulphuric acid and then with MOH to give the --OSO₃ M group.Alternatively a chloroalkyl group in the dye could be reacted with K₂SO₃ to give the --CH₂ SO₃ K group. Also, sulphonation of an aromaticring or other reactive group in the dye with a sulphonating agent suchas H₂ SO₄ or Cl--SO₃ H would give the solubilizing group. Such groupscould also be present in the coupling component prior to diazotisationand coupling.

The following Preparations, Example and tables will illustrate themaking and use of intermediates for the synthesis of dyes of the presentinvention.

PREPARATION A--α-(N-Ethylanilino)-Toluenesulfonic Acid

To a 30.0 g. of 100% sulfuric acid is added N-benzyl-N-ethylaniline(30.0 g.) dropwise below about 50° C. To this solution is added, at50°-60° C., 60% oleum (30.0 g.) with good stirring. The mixture isstirred and heated at about 60° C. for three hours and then drowned into200 ml. of water. The free sulfonic acid which is mostly the meta isomerwith a small amount of para, precipitates on standing and is collectedby filtration, washed with water, and dried. N-Benzylines containinggroups such as alkyl, alkoxy, and halogen in the ortho, meta, or parapositions of the benzyl group may also be sulfonated by this procedure.The exact location of the sulfonic acid group in these cases is oftennot known and mixtures usually are produced.

Aromatic amines which contain N-aralkyl groups and which are sulfonatedby the above procedure to give Couplers 2 to 11 are listed below.

    ______________________________________                                        COUPLER NO.                                                                   ______________________________________                                        2            N--Benzyl-N--ethyl-m-toluidine;                                  3            N--Benzyl-2,7-dimethyl-1,2,3,4-                                               tetrahydroquinoline;                                             4            N--Benzyl-2,3-dihydro-3,6-dimethyl-                                           1,4-benzoxazine;                                                 5            N--Methyl-N--(2-phenylethyl)aniline;                             6            N--Ethyl-N--(4-phenylbutyl)-3-                                                chloroaniline;                                                   7            N,N--Dibenzylaniline;                                            8            N--Benzyl-2,5-dimethylaniline;                                   9            N--Benzyl-2-methoxy-5-methylaniline;                             10           N--Benzyl-2-methoxy-5-chloroaniline;                                          and                                                              11           N--Benzyl-N--cyclohexylaniline.                                  ______________________________________                                    

PREPARATION B--Diazotization and Coupling of 2,6-dibromo-4-acetylaniline

To 150 g. of 60% acetic acid containing 10 g. of concentrated H₂ SO₄ isadded 8.2 g. (0.055 m.) of 2,6-dibromo-4-acetylaniline at roomtemperature. The solution is cooled to -5° C., and a solution of 3.6 g.NaNO₂ in 20 ml. of concentrated H₂ SO₄ is added below 0° C. The reactionmixture is stirred at -5° to 0° C. for 1.5 hours. Each of the Couplers 1to 11 (0.005 m.) is added to water, or a 0.005 mole aliquot of thecoupler in dilute sulfuric acid is added to water, and cooled in an icebath.

To each chilled coupler is added a 0.005 mole aliquot of the diazoniumsolution. The coupling mixture is treated with enough potassium acetateto neutralize the mineral acid. Water is added to the coupling mixtureto a total volume of about 200 ml. and the dyes collected by filtration,washed with 10% KCl solution, and dried in air. The dyes usually areadmixed with about an equal weight of K₂ SO₄ and are used for dyeingwithout further purification to produce red shades on polyamides. Thesedyes are intermediates for the preparation of dyes of the presentinvention.

PREPARATION C--Sulfonation of Dye Containing an N-Aralkylamino Group

The dye from 2,6-dibromo-4-acetylaniline N-benzyl-N-ethylaniline (1.5g.) is added portionwise to 15 ml. of concentrated H₂ SO₄ over 20 min.,allowing the temperature to rise to 30° C. The reaction mixture is thenheated at 70° C., when the reaction is completed as evidenced bythin-layer chromatography. After the reaction mixture is drowned onice-water mixture, 50% NaOH is added until the pH is about 7. The dye iscollected by filtration, washed with water, and dried in air. Thestructure is as follows: ##STR3##

EXAMPLE ##STR4##

A mixture of compound (I) (2 g.), benzaldehyde (1.5 g.), acetic acid (25ml.) and concentrated sulphuric acid (5 ml.) was stirred at 100° C. for1.5 hours. The reaction mixture was poured into cold water and theproduct dye (II) filtered off, washed with water and dried. Compound (I)had previously been prepared by diazotising the known2,6-dibromo-4-acetylaniline and coupling withN-ethyl-2,2,4,7-tetra-methyl-1,2,3,4-tetrahydroquinoline by knownprocedures. The dye (II) when applied to nylon, polyester and othersynthetic fibres by known techniques gave bright, bluish red shades withgood dyeing and fastness properties.

By using the methods described hereinabove, the following dyes areobtained.

    TABLE 1      ##STR5##       Cinnamoyl Group   Substituents    Position R.sub.1 on D R.sub.5 on A     R.sub.1 on C R.sub.2 R.sub.7       4 H H H H H H 4 4-NO.sub.2 H 6-COCH.sub.3 2-CH.sub.3 C.sub.2 H.sub.5     Ph 4 4-CN H 6-NO.sub.2 5-COCH.sub.3 C.sub.2 H.sub.5 C.sub.6 H.sub.11 4     5-COCH.sub.3 H 5,6-di-Cl 5-OCH.sub.3 CH.sub.2C.sub.6 H.sub.4-p-SO.sub. 4     K CH.sub.2CHCH.sub.2 4 4-COPh CH.sub.3 6-CN 5-SO.sub.3 Na H CH.sub.2     OOCC.sub.2 H.sub.5 5 2,4-di-COOH CH.sub.3 4-NHSO.sub.2      CH.sub.3 5-OCH.sub.2 CH.sub.2 SO.sub.4 K CH.sub.2C.sub.6      H.sub.104-SO.sub.3 K C.sub.6 H.sub.4-p-OOCCH.sub.3 6 4-OOCCH.sub.3     CH.sub.3 5-CH.sub.3 5-OCH.sub.2 CH.sub.2 SO.sub.4 NH(Et).sub.3 H C.sub.6     H.sub.104-CH.sub.3 4 4-NHCOCH.sub.3 CH.sub.3 6-OCH.sub.3 2-CH.sub.3     CH.sub.2C.sub.6 H.sub.4-p-SO.sub.4 NH(Et).sub.3 CH.sub.2 CH.sub.2     (C.sub.4 H.sub.4 O.sub.2 N) 6 4-NHCOPh CH.sub.3 4-Ph 2-Ph CH.sub.3     CH.sub.2 CH.sub.2 NO.sub.2 4 4-C.sub.2 H.sub.5 CH.sub.3 H 2-NO.sub.2     CH.sub.3 C.sub.6 H.sub.4-p-NO.sub.2 6 4-Ph H H 2-OCH.sub.3 CH.sub.3     CH.sub.2 NHOCCH.sub.3 4 Cl H 5,6-di-SO.sub.3 Na 5-NHCOCH.sub.3 C.sub.2     H.sub.5 CH.sub.2 NHSO.sub.2 CH.sub.3 4 SO.sub.3 K H H 3NHCOCH.sub.3 H     C.sub.2 H.sub.5 4 2-Cl4-SO.sub.2 CH.sub.3 H 6-SO.sub.3 Na 3-NHSO.sub.2     CH.sub.3 C.sub.2 H.sub.5 C.sub.6 H.sub.4-p-NHOCCH.sub.3 4 4-NHSO.sub.2     CH.sub.3 H 6-OCH.sub.2 CH.sub.2 SO.sub.4 K 3-COOCH.sub.3 C.sub.2 H.sub.5     C.sub.6 H.sub.4-p-NHSO.sub.2 CH.sub.3 4 4-COOCH.sub.3 H 6-OCH.sub.2     CH.sub.2 SO.sub.4 K 3-COOH C.sub.2 H.sub.5 C.sub.6      H.sub.104-NHOOCH.sub.3 4 2-OCH.sub.3 C.sub.2 H.sub.5 6-NHCOPh 2-Cl     CH.sub.2 CH.sub.2 Cl CH.sub.2 CH.sub.2 Cl 5 4-OC.sub.2 H.sub.5 C.sub.2     H.sub.5 4-NHCOPh 2,6-di-Br C.sub.6 H.sub.4-p-Br C.sub.6 H.sub.4-p-Br 6     4-SO.sub.3 Na C.sub.2 H.sub.5 4-NHCOCH.sub.3 2,6-di-Br C.sub.6      H.sub.4-p-CN C.sub.6 H.sub.4-p-CN 6 2-SO.sub.3 Na C.sub.2 H.sub.5     4-OOCC.sub.2 H.sub.5 2-OCH.sub.35-NHCOCH.sub.3 CH.sub.2 CH.sub.2 CN     CH.sub.2 CH.sub.2 CN 4 2-OCH.sub.34-SO.sub.3 K H 5-COOH 2-CH.sub.2     OOCCH.sub.3 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OC.sub.     2 H.sub.5 4 4-OCH.sub.2 CH.sub.2 OSO.sub.3 K H H 2-CH.sub.2 Cl CH.sub.2     CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OCH.sub.2     CH.sub.2 OC.sub.2 H.sub.5 4 2-SO.sub.3 Na5-Cl H H 2-CN CH.sub.2 Ph     CH.sub.2C.sub.6 H.sub.4-p-SO.sub.4 N.sup.+ H(CH.sub.3).sub.3 4 4-Cl H     6-SO.sub.2 CH.sub.3 2-OOCCH.sub.3 CH.sub.2 C.sub.6 H.sub.11 CH.sub.2     C.sub.6 H.sub.10 4-SO.sub.3 Na 4 4-OH H 6-CF.sub.3 5-COOH H C.sub.6     H.sub.4-o-OH 4 4-CH.sub.2 OOCCH.sub.3 C.sub.3 H.sub.7n 6-COOCH.sub.3     5-OH C.sub.2 H.sub.5CH.sub.2 CH.sub.2 OH 4 4-SO.sub.3 K C.sub.3 H.sub.7n     6-CHO 5-CH.sub.2 CHCH.sub.2 CH.sub.2 CH.sub.2SO.sub.3 K CH.sub.2         S     CH.sub.2O.sub.3 K 6 4-OPh H 4-CONH.sub.2 2-CH.sub.3 H CH.sub.2C.sub.6     H.sub.4-p-OSO.sub.3 K 6 4-NO.sub.2 H 4-CONHCH.sub.3 5-COCH.sub.3 H     CH.sub.2 OPh 6 5-CN H 4-CH.sub.2 Ph 5-OCH.sub.3 H CH.sub.2 SO.sub.2 NHPh     4 4-SO.sub.3 K H H 3-CH.sub.3 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 SO.sub.3     K 4 4-COCH.sub.3 H 6-CH.sub.2 SO.sub.3 K 5-SO.sub.3 Na CH.sub.2 SO.sub.2     NHCH.sub.3 CH.sub.2 SO.sub.2 NHCH.sub.3 4 5-CH.sub.3 H 6-CH.sub.2     OSO.sub.3 K 5-OCH.sub.2 CH.sub.2 SO.sub.4 K H CH.sub.2C.sub.6      H.sub.4-p-SO.sub.2 NHCH.sub.3 4 5-C.sub.6 H.sub.4-p-SO.sub.3 K H     6-C.sub.6 H.sub.4-p-SO.sub.3 K 5-OCH.sub.2 CH.sub.2 SO.sub.3 K CH.sub.2     COOCH.sub.3 CH.sub.2 COOCH.sub.3 4 5-OCH.sub.3 H 6-CH.sub.2 CH.sub.2 OH     2-CH.sub.3 H CH.sub.2 SO.sub.2      N(CH.sub.3).sub.2 4 4,5-di-Br H 6-CH.sub.2 Cl 2-C.sub.6      H.sub.4-p-SO.sub.3 K C.sub.2 H.sub.5 C.sub.6 H.sub.4-p-NHCOOCH.sub.3 4     5-COOH C.sub.4 H.sub.9n 6-C.sub.6 H.sub.4-p-Br 2-NO.sub.2 C.sub.2     H.sub.5 CH.sub.2 CH.sub.2 CONH.sub. 2 4 H H H 2-OCH.sub.3 C.sub.2     H.sub.5 C.sub.6 H.sub.4-p-CONHCH.sub.3 4 4-NO.sub.2 H 5-COCH.sub.3     5-NHCOCH.sub.3 C.sub.2 H.sub.5 C.sub.6 H.sub.4-p-SCH.sub.3 4 4-CN H     5-NO.sub.2 3-NHSO.sub.2 CH.sub.3 CH.sub.2 CH.sub.2 SCH.sub.3 CH.sub.2     CH.sub.2 SCH.sub.3 4 5-COCH.sub.3 H 5-Cl 3-COOCH.sub.3 H CH.sub.2C.sub.6     H.sub.4-p-SCH.sub.3 4 4-COPh CH.sub.3 5,6-di-CN 3-COOH CH.sub.2 SO.sub.2     C.sub.2 H.sub.5 CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 4 2,4-di-COOH CH.sub.3     5-NHSO.sub.2 CH.sub.3 2-Cl H CH.sub.2 SO.sub.2 Ph 4 4-OOCCH.sub.3     CH.sub.3 6-CH.sub.3 2,6-di-Br H CH.sub.2 CH.sub.2 OSO.sub.3      K 4 4-NHCOCH.sub.3 CH.sub.3 6-OCH.sub.3 2,6-di-Br H C.sub.6      H.sub.4-p-OSO.sub.3      K 4 4-NHCOPh CH.sub.3 6-Ph 2-OCH.sub.35-NHCOCH.sub.3 H CH.sub.2     (C.sub.8 H.sub.4 O.sub.2 N) 4 4-CH.sub.2 CHCH.sub.2 H H 3-NHCOCH.sub.3     C.sub.2 H.sub.5 C.sub.2 H.sub.5 4,6 H CH.sub.3 H 3-OCPh C.sub.2 H.sub.5     C.sub.2 H.sub.5 4 4-SO.sub.3 K H H 2-OCH.sub.35-NHCOCH.sub.3 C.sub.2     H.sub.5 CH.sub.2 CH.sub.2 SO.sub.3 K 4 4-CONH.sub.2 H H 5-CH.sub.2     CONHCH.sub.3 H H 4 3-SO.sub.2 NH.sub.2 H 6-COCH.sub.3 5-CH.sub.2     CON(CH.sub.3).sub.2 C.sub.2 H.sub.5 Ph 4 4-SO.sub.2 NHCH.sub.3 H     6-NO.sub.2 5-CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5     C.sub.2 H.sub.5 C.sub.6 H.sub.11 4 4-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 H     6-Cl 5-CH.sub.2 SC.sub.2 H.sub.5 H CH.sub.2CHCH.sub.2 4 4-SO.sub.3     C.sub.6 H.sub.5 CH.sub.3 6-CN 2-CH.sub.2 SC.sub.6 H.sub.5 H CH.sub.2     OOCC.sub.2 H.sub.5 4 4-SCH.sub.3 CH.sub.3 6-NHSO.sub.2      CH.sub.3 5-CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 H C.sub.6      H.sub.4-p-OOCCH.sub.3 4 2,4-di-SCN CH.sub.3 5-CH.sub.3 5-CH.sub.2     SO.sub.2 C.sub.6 H.sub.5 H C.sub.6 H.sub.104-CH.sub.3 4 4-SO.sub.2     C.sub.6 H.sub.5 CH.sub.3 5-OCH.sub.3 5-C.sub.6 H.sub.3 -o,-p-di-CN H     CH.sub.2 CH.sub.2 (C.sub.4 H.sub.4 O.sub.2 N) 4 2-CHO4-CN CH.sub.3 6-Ph     5-C.sub.6 H.sub.2-o,.sub.--m,-p-tri-Cl CH.sub.3 CH.sub.2 CH.sub.2     NO.sub.2 4 4-CONHC.sub.2 H.sub.5 CH.sub.3 H 2,6-di-OSO.sub.3      N H(CH.sub.3).sub.3 CH.sub.3 C.sub.6 H.sub.4-p-NO.sub.2 4 4-CON(C.sub.2     H.sub.5).sub.2 H H 2,6-di-SO.sub.3 N H(CH.sub.3).sub.3 CH.sub.3 CH.sub.2     NHOCCH.sub.3 4 3-C.sub.6 H.sub.11 H 6-SO.sub.3 Na 2,6-di-OSO.sub.3 K     C.sub.2 H.sub.5 CH.sub.2 NHSO.sub.2 CH.sub.3 4 3-SC.sub.6 H.sub.5 H     6-SO.sub.3 Na 2-SO.sub.3 N H(CH.sub.3).sub.3 C.sub.2 H.sub.5 C.sub.6     H.sub.4-p-NHOCCH.sub.3 4 4-NHSO.sub.2 C.sub.6 H.sub.5 H 5-OCH.sub.2     CH.sub.2 SO.sub.4 K 2-OSO.sub.3 N H(CH.sub.3).sub.3 C.sub.2 H.sub.5     C.sub.6 H.sub.4-p-NHSO.sub.2 CH.sub.3 4 4-SC.sub.6      H.sub.11 H 5-OCH.sub.2 CH.sub.2 SO.sub.4 K 5-SC.sub.6      H.sub.10-p-SO.sub.3 K C.sub.2 H.sub.5 C.sub.6 H.sub.104-NHOCCH.sub.34     4-C.sub.6 H.sub.4-p-CH.sub.3 C.sub.2 H.sub.5 6-NHCOPh 5-C.sub.6      H.sub.4-p-CH.sub.3 CH.sub.2 CH.sub.2 Cl CH.sub.2 CH.sub.2      Cl 4 4-C.sub.6 H.sub.4-p-CH.sub.2 CHCH.sub.2 C.sub.2 H.sub.5 6-NHCOPh     5-C.sub.6 H.sub.4-p-CH.sub.2 CHCH.sub.2 C.sub.6 H.sub.4-p-Br C.sub.6     H.sub.4-p-Br 4 4-OCH.sub.2 CH.sub.2 NO.sub.2 C.sub.2      H.sub.5 5-NHCOCH.sub.3 5-OCH.sub.2 CH.sub.2 NO.sub.2 C.sub.6      H.sub.4-p-CN C.sub.6 H.sub.4-p-CN 4 2-CH.sub.2 NHCOCH.sub.3 C.sub.2     H.sub.5 5-OOCC.sub.2 H.sub.5 2-CH.sub.2 NHCOCH.sub.3 CH.sub.2 CH.sub.2     CN CH.sub.2 CH.sub.2 CN 4 4-CH.sub.2 NHSO.sub.2 C.sub.2 H.sub.5 H 6-COOH     5-CH.sub.2 NHSO.sub.2 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.     5 CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 4,6 4-CH.sub.2 CH.sub.2 Cl H H     5-CH.sub.2 CH.sub.2 Cl CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2     H.sub.5 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2      H.sub.5 6 2,6-di-CH.sub.2 CN H H 2,6-di-CH.sub.2 CN CH.sub.2 Ph     CH.sub.2 Ph 6 4-CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 H 4-SO.sub.2 CH.sub.3     5-CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 CH.sub.2 C.sub.6 H.sub.11 CH.sub.2     C.sub.6 H.sub.11 6 4-CH.sub.2 C.sub.6 H.sub.5 H 4-CH.sub.2 C.sub.6     H.sub.5 5-COOH H C.sub.6 H.sub.4-o-OH 6 4-CH.sub.2 C.sub.6 H.sub.11     C.sub.3 H.sub.7n 4-COOCH.sub.3 5-CH.sub.2 C.sub.6 H.sub.11 C.sub.2     H.sub.5 CH.sub.2 CH.sub.2 OH 6 4-CH.sub.2 CH(OH)CH.sub.2 OH C.sub.3     H.sub.7n 4-CHO 5-CH.sub.2 CH(OH)CH.sub.2 OH CH.sub.2 CH.sub.2SO.sub.3 K     CH.sub.2 CH.sub.2SO.sub.3 K 4 4-CH.sub.2 CH.sub.2SO.sub.3      K H 5-CONH.sub.2 5-CH.sub.2 CH.sub.2SO.sub.3 K H C.sub. 6      H.sub.4-p-OSO.sub.3 K 4 4-CH.sub.2 OC.sub.6 H.sub.5 H 5-CONHCH.sub.3     5-CH.sub.2 OC.sub.6 H.sub.5 H CH.sub.2 OPh 4 4-CH.sub.2 OOCC.sub.6     H.sub.5 H 5-CH.sub.2 Ph 5-CH.sub.2 OOCC.sub.6 H.sub.5 H CH.sub.2     SO.sub.2 NHPh 4 5-CH.sub.2 COOCH.sub.3 H 6-CH.sub.2 SO.sub.3      K 5-CH.sub.2 COOCH.sub.3 CH.sub.2 SO.sub.2 NHCH.sub.3 CH.sub.2 SO.sub.2     NHCH.sub.3 4 4-C.sub.6 H.sub.4-p-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 H     6-CH.sub.2 OSO.sub.3 K 5-C.sub.6 H.sub.4-p-SO.sub.2 N(C.sub.2      H.sub.5).sub.2 H C.sub.6 H.sub.4-p-SO.sub.2 NHCH.sub.3 4 CH.sub.2     CH.sub.2 NHCOOCH.sub.3 H 6-C.sub.6 H.sub.4-p-SO.sub.3 K 5-CH.sub.2     CH.sub.2 NHCOOCH.sub.3 CH.sub.2 COOCH.sub.3 CH.sub.2 COOCH.sub.3 4     4-CH.sub.2 NHCONHCH.sub.3 H 6-CH.sub.2 CH.sub.2 OH 5-CH.sub.2      NHCONHCH.sub.3 H CH.sub.2 SO.sub.2 N(CH.sub.3).sub.2 4 4-CH.sub.2     CONH.sub.2 H 6-CH.sub.2 Cl 5-CH.sub.2 CONH.sub.2 C.sub.2 H.sub.5 C.sub.6     H.sub.4-p-NHCOOCH.sub.3 4 5-CH.sub.2 CONHCH.sub.3 C.sub.4 H.sub.9n     6-C.sub.6 H.sub.4-p-Br 5-CONH.sub.2 C.sub.2 H.sub.5 CH.sub.2 CH.sub.2     CONH.sub.2 4 4-CH.sub.2 CON(CH.sub.3).sub.2 H H 3-SO.sub.2 NH.sub.2     C.sub.2 H.sub.5 C.sub.6 H.sub.4-p-CONHCH.sub.3 4 4-CH.sub.2 CH.sub.2     OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 H 5-COCH.sub.3 5-SO.sub.2 NHCH.sub.3     C.sub.2 H.sub.5 C.sub.6 H.sub.4-p-SCH.sub.3 4,6 4-CH.sub.2 SC.sub.2     H.sub.5 H 5-NO.sub.2 5-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.2     CH.sub.2 SCH.sub.3 CH.sub.2 CH.sub.2 SCH.sub.3 6 5-CH.sub.2 SC.sub.6     H.sub.5 H 4-Cl 5-SO.sub.3 C.sub.6 H.sub.5 H CH.sub.2C.sub.6      H.sub.4-p-SCH.sub.3 4 4-CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 CH.sub.3 6-CN     5-SCH.sub.3 CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 CH.sub.2 SO.sub.2 C.sub.2     H.sub.5 4 2,4-di-CH.sub.2 SO.sub. 2 C.sub.6      H.sub.5 CH.sub.3 6-NHSO.sub.2 CH.sub.3 2,5-di-SCN H CH.sub.2 SO.sub.2     Ph 4 4-C.sub.6 H.sub.3-o,-p-di-CN CH.sub.3 5-CH.sub.3 5-SO.sub.2 C.sub.6     H.sub.5 H CH.sub.2 CH.sub.2 OSO.sub.3 K 4 4-C.sub.6      H.sub.2-o,-m,-p-tri-Cl CH.sub.3 5-OCH.sub.3 2-CHO6-CN H C.sub.6         p     H.sub.4--OSO.sub.3 K 4 2,6-di-OSO.sub.3 Na CH.sub.3 6-Ph 5-CONHC.sub.2     H.sub.5 H CH.sub.2(C.sub.8 H.sub.4 O.sub.2 N) 4 H H 6-CH.sub.2 (C.sub.4     H.sub.4 O.sub.2 N) 5-CON(C.sub.2 H.sub.5).sub.2 C.sub.2 H.sub.5 C.sub.2     H.sub.5 4 H H 6-CH.sub.2 (C.sub.4 H.sub.3 O) 3-C.sub.6 H.sub.11 C.sub.2     H.sub.5 C.sub.2 H.sub.5 4 5-CH.sub.2 (C.sub.8 H.sub.4 O.sub.2 N) H H     3-SC.sub.6 H.sub.5 C.sub.2 H.sub.5 C.sub.2 H.sub.5 4 5-CH.sub.2 (C.sub.4     H.sub.3 O) H H 6-NHSO.sub.2 C.sub.6 H.sub.5 C.sub.2 H.sub.5 C.sub. 2     H.sub.5 4 2-Cl,SO.sub.3 M H 2,6-di-Br 2-OCH.sub.35-CH.sub.3 H C.sub.2     H.sub.5 4 H H 2,6-di-Br 2-OCH.sub.35-CH.sub.3 H C.sub.2      H.sub.5

    TABLE 2      ##STR6##       Cinnamoyl Group   Substituents      Position R.sub.1 on D R.sub.5 on A     R.sub.1 on C R.sub.3 R.sub.4 R.sub.8 R.sub.7       4 H H H H H H H H 4 4-NO.sub.2 H 5-COCH.sub.3 7-CH.sub.3 CH.sub.3     CH.sub.3 CH.sub.3 Ph 4 4-CN H 5-NO.sub.2 5-COCH.sub.3 CH.sub.3 CH.sub.3     H C.sub.6 H.sub.11 4 5-COCH.sub.3 H 5-Cl 5-OCH.sub.3 CH.sub.3 CH.sub.3 H     CH.sub.2CHCH.sub.2 4,5 4-COPh CH.sub.3 6-CN 7-SO.sub.3 Na CH.sub.3     CH.sub.3 H CH.sub.2 OOCC.sub.2      H.sub.5 5 2,4-di-COOH CH.sub.3 4-NHSO.sub.2 CH.sub.3 7-OCH.sub.2     CH.sub.2 SO.sub.4 K CH.sub.3 CH.sub.3 H C.sub.6 H.sub.4-p-OOCCH.sub.3 6     4-OOCCH.sub.3 CH.sub.3 5-CH.sub.3 7-OCH.sub.2 CH.sub.2 SO.sub.4 N     H(Et).sub.3 CH.sub.3 CH.sub.3 H C.sub.6      H.sub.104-CH.sub.3 6 4-NHCOCH.sub.3 CH.sub.3 4,5-di-OCH.sub.3 7-CH.sub.3      CH.sub.3 H H CH.sub.2 CH.sub.2 (C.sub.4 H.sub.4 O.sub.2 N) 6 4-NHCOPh     CH.sub.3 4-Ph 7-Ph CH.sub.3 H H CH.sub.2 CH.sub.2 NO.sub.2 4 4-C.sub.2     H.sub.5 CH.sub.3 H 7-NO.sub.2 CH.sub.3 H H C.sub.6 H.sub.4-p-NO.sub.2 6     4-Ph H H 7-OCH.sub.3 CH.sub.3 H H CH.sub.2 NHOCCH.sub.3 4 2,5-di-Cl H     6-SO.sub.3 Na 7-NHCOCH.sub.3 CH.sub.3 H H CH.sub.2 NHSO.sub.2 CH.sub.3 4     2-Cl4-SO.sub.2 CH.sub.3 H 6-SO.sub.3 Na 7-NHSO.sub.2 CH.sub.3 CH.sub.3 H     H C.sub.6 H.sub.4-p-NHOCCH.sub.3 4 4-NHSO.sub.2 CH.sub.3 H 5-OCH.sub.2     CH.sub.2 SO.sub.4 K 7-COOCH.sub.3 CH.sub.3 C.sub.2 H.sub.5 C.sub.2     H.sub.5 C.sub.6 H.sub.4-p-NHSO.sub.2      CH.sub.3 4 4-COOCH.sub.3 H 5-OCH.sub.2 CH.sub.2 SO.sub.4 K 7-COOH H H H     C.sub.6 H.sub.104-NHOCCH.sub.3 4 2-OCH.sub.3 C.sub.2 H.sub.5 6-NHCOPh     7-Cl CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 Cl 4 4-OC.sub.2     H.sub.5 C.sub.2 H.sub.5 6-NHCOPh 5,7-di-Br CH.sub.3 CH.sub.3 H C.sub.6     H.sub.4-p-Br 4 4-SO.sub.3 Na C.sub.2 H.sub.5 6-NHCOCH.sub.3 5,7-di-Br     CH.sub.3 CH.sub.3 H C.sub.6 H.sub.4-p-CN 4 2-SO.sub.3 Na C.sub.2 H.sub.5     5-OOCC.sub.2 H.sub.5 5-OCH.sub.37-NHCOCH.sub.3 CH.sub.3 CH.sub.3 H     CH.sub.2 CH.sub.2 CN 4 2-OCH.sub.34-SO.sub.3 K H 6-COOH 7-CH.sub.2     OOCCH.sub.3 CH.sub.3 CH.sub.3 H CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 4     4-OCH.sub.2 CH.sub.2 OSO.sub.3 K H H 7-CH.sub.2 Cl CH.sub.3 CH.sub.3 H     CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 4 2-SO.sub.3     Na5-Cl H H 7-CN CH.sub.3 H H CH.sub.2 Ph 4 4-Cl H 5-SO.sub.2 CH.sub.3     7-OOCCH.sub.3 CH.sub.3 H H CH.sub.2 C.sub.6 H.sub.11 4 4-OH H 5-CF.sub.3     5-COOH CH.sub.3 H H C.sub.6 H.sub.4-o-OH 4 4-CH.sub.2 OOCCH.sub.3     C.sub.3 H.sub.7n 5-COOCH.sub.3 5-OH CH.sub.3 H H CH.sub.2 CH.sub.2 OH 4     4-SO.sub.3 K C.sub.3 H.sub.7n 5-CHO 5-CH.sub.2 CHCH.sub.2 CH.sub.3 H H     CH.sub.2 CH.sub.2SO.sub.3 K 4,6 4-OPh H 5-CONH.sub.2 7-CH.sub.3 CH.sub.3     H H C.sub.6 H.sub.4-p-OSO.sub.3      K 6 4-NO.sub.2 H 4-CONHCH.sub.3 7-COCH.sub.3 CH.sub.3 C.sub.2 H.sub.5     C.sub.2 H.sub.5 CH.sub.2 OPh 4 5-CN H 5-CH.sub.2 Ph 7-OCH.sub.3 H H H     CH.sub.2 SO.sub. 2 NHPh 4 4-COCH.sub.3 H 5-CH.sub.2 SO.sub.3      K 7-SO.sub.3 Na CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.2 SO.sub.2 NHCH.sub.3     4 5-CH.sub.3 H 5-CH.sub.2 OSO.sub.3 K 7-OCH.sub.2 CH.sub.2 SO.sub.4 K     CH.sub.3 CH.sub.3 H C.sub.6 H.sub.4-p-SO.sub.2 NHCH.sub.3 4 5-Ph H     5-C.sub.6 H.sub.4-p-SO.sub.3 K 7-OCH.sub.2 CH.sub.2 SO.sub.3 K CH.sub.3     CH.sub.3 H CH.sub.2 COOCH.sub.3 4 5-OCH.sub.3 H 5-CH.sub.2 CH.sub.2 OH     7-CH.sub.3 CH.sub.3 CH.sub.3 H CH.sub.2 SO.sub.2 N(CH.sub.3).sub.2 4     4,5-di-Br H 5-CH.sub.2 Cl 7-Ph CH.sub.3 CH.sub.3 H C.sub.6      H.sub.4-p-NHCOOCH.sub.3 4 5-COOH C.sub.4 H.sub.9n 6-C.sub.6      H.sub.4-p-Br 7-NO.sub.2 H H H CH.sub.2 CH.sub.2 CONH.sub.2 4 H H H     7-OCH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3 C.sub.6 H.sub.4-p-CONHCH.sub.3 4     4-NO.sub.2 H 6-COCH.sub.3 7-NHCOCH.sub.3 CH.sub.3 CH.sub.3 H C.sub.6     H.sub.4-p-SCH.sub.3 4 4-CN H 6-NO.sub.2 7-NHSO.sub.2 CH.sub.3 CH.sub.3     CH.sub.3 H CH.sub.2 CH.sub.2      SCH.sub.3 4 5-COCH.sub.3 H 6-Cl 7-COOCH.sub.3 CH.sub.3 CH.sub.3 H     CH.sub.2C.sub.6 H.sub.4-p-SCH.sub.3 4 4-COPh CH.sub.3 6-CN 7-COOH     CH.sub.3 CH.sub.3 H CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 4 2,4-di-COOH     CH.sub.3 5-NHSO.sub.2 CH.sub.3 7-Cl CH.sub.3 CH.sub.3 H CH.sub.2     SO.sub.2 Ph 4 4-OOCCH.sub.3 CH.sub.3 6-CH.sub.3 5,7-di-Br CH.sub.3 H H     CH.sub.2 CH.sub.2 OSO.sub.3 K 4 4-NHCOCH.sub.3 CH.sub.3 6-OCH.sub.3     5,7-di-Br CH.sub.3 H H C.sub.6 H.sub.4-p-OSO.sub.3 K 4 4-NHCOPh CH.sub.3     6-Ph 5-OCH.sub.37-NHCOCH.sub.3 CH.sub.3 H H CH.sub.2 (C.sub.8 H.sub.4     O.sub.2 N) 5 4-CH.sub.2 CHCH.sub.2 H H 7-NHCOCH.sub.3 C.sub.2 H.sub.5 H     H C.sub.2 H.sub.5 4 H CH.sub.3 H 7-OCPh C.sub.2 H.sub.5 H H C.sub.2     H.sub.5 4,6 4-CONH.sub.2 H H 7-CH.sub.2      CONHCH.sub.3 H H H H 6 3-SO.sub.2 NH.sub.2 H 4-COCH.sub.3 7-CH.sub.3     CON(CH.sub.3).sub.2 CH.sub.3 CH.sub.3 CH.sub.3 Ph 6 4-SO.sub.2      NHCH.sub.3 H 4-NO.sub.2 7-CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2     H.sub.5 CH.sub.3 CH.sub.3 H C.sub.6 H.sub.11 6 4-SO.sub.2 N(C.sub.2     H.sub.5).sub.2 H 4-Cl 7-CH.sub.2 SC.sub.2 H.sub.5 CH.sub.3 CH.sub.3 H     CH.sub.2CHCH.sub.2 4 4-SO.sub.3 C.sub.6 H.sub.5 CH.sub.3 6-CN 7-CH.sub.2     SC.sub.6 H.sub.5 CH.sub.3 CH.sub.3 H CH.sub.2 OOCC.sub.2 H.sub.5 5     4-SCH.sub.3 CH.sub.3 4-NHSO.sub.2 CH.sub.3 7-CH.sub.2 SO.sub.2 C.sub.2     H.sub.5 CH.sub.3 CH.sub.3 H C.sub.6 H.sub.4-p-OOCCH.sub.3 4 2,4-di-SCN     CH.sub.3 6-CH.sub.3 7-CH.sub.2 SO.sub.2 C.sub.6 H.sub.5 CH.sub.3     CH.sub.3 H C.sub.6 H.sub.104-CH.sub.3 4 4-SO.sub.2 C.sub.6 H.sub.5     CH.sub.3 6-OCH.sub.3 7-C.sub.6 H.sub.3-o,-p-di-CN CH.sub.3 H H CH.sub.2     CH.sub.2(C.sub.4 H.sub.4 O.sub.2 N) 4 2-CHO4-CN CH.sub.3 6-Ph 7-C.sub.6     H.sub.2-o,-m,-p-tri-Cl CH.sub.3 H H CH.sub.2 CH.sub.2 NO.sub.2 4     4-CONHC.sub.2 H.sub.5 CH.sub.3 H 5,7-di-OSO.sub.3 NH(CH.sub.3).sub.3     CH.sub.3 H H C.sub.6 H.sub.4-p-NO.sub.2 4 4-CON(C.sub.2 H.sub.5).sub.2 H     H 5,7-di-OSO.sub.3 Na CH.sub.3 H H CH.sub.2 NHOCCH.sub.3 4 3-C.sub.6     H.sub.11 H 6-SO.sub.3 Na 5,7-di-SO.sub.3 NH(CH.sub.3).sub.3 CH.sub.3 H H     CH.sub.2 NHSO.sub.2 CH.sub.3 4 3-SC.sub.6 H.sub.5 H 6-SO.sub.3 Na     7-OSO.sub.3 NH(CH.sub.3).sub.3 CH.sub.3 H H C.sub.6      H.sub.4-p-NHOCCH.sub.3 4 4-NHSO.sub.2 C.sub.6 H.sub.5 H 6-OCH.sub.2     CH.sub.2 SO.sub.4 K 5,7-di-OSO.sub.3 Na CH.sub.3 C.sub.2 H.sub.5 C.sub.2     H.sub.5 C.sub.6 H.sub.4-p-NHSO.sub.2 CH.sub.3 4 4-SC.sub.6 H.sub.11 H     6-OCH.sub.2 CH.sub.2 SO.sub.4 K 7-SC.sub.6 H.sub.11 H H H C.sub.6     H.sub.104-NHOCCH.sub.3 4 4-C.sub.6 H.sub.4-p-CH.sub.3 C.sub.2 H.sub.5     6-NHCOPh 7-C.sub.6 H.sub.4-p-CH.sub.3 CH.sub.3 CH.sub.3 CH.sub.3     CH.sub.2 CH.sub.2 Cl 5 4-C.sub.6 H.sub.4-p-CH.sub.2 CHCH.sub.2 C.sub.2     H.sub.5 4-NHCOPh 7-C.sub.6 H.sub.4-p-CH.sub.2 CHCH.sub.2 CH.sub.3     CH.sub.3 H C.sub.6 H.sub.4-p-Br 6 4-OCH.sub.2 CH.sub.2 NO.sub.2 C.sub.2     H.sub.5 4-NHCOCH.sub.3 7-OCH.sub.2 CH.sub.2 NO.sub.2 CH.sub.3 CH.sub.3 H     C.sub.6 H.sub.4-p-CN 6 2-CH.sub.2 NHCOCH.sub.3 C.sub.2      H.sub.5 4-OOCC.sub.2 H.sub.5 7-CH.sub.2 NHCOCH.sub.3 CH.sub.3 CH.sub.3     H CH.sub.2 CH.sub.2 CN 4 4-CH.sub.2 NHSO.sub.2 C.sub.2 H.sub.5 H 5-COOH     7-CH.sub.2 NHSO.sub.2 C.sub.2 H.sub.5 CH.sub.3 CH.sub.3 H CH.sub.2     CH.sub.2 OC.sub.2 H.sub.5 4,6 4-CH.sub.2 CH.sub.2 Cl H H 7-CH.sub.2     CH.sub.2 Cl CH.sub.3 CH.sub.3 H CH.sub.2 CH.sub. 2 OCH.sub.2 CH.sub.2     OC.sub.2 H.sub.5 6 2,6-di-CH.sub.2 CN H H 5,7-di-CH.sub.2 CN CH.sub.3 H     H CH.sub.2 Ph 6 4-CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 H 4-SO.sub.2     CH.sub.3 7-CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 CH.sub.3 H H CH.sub.2     C.sub.6 H.sub.11 4 4-CH.sub.2 C.sub.6 H.sub.5 H 6-CH.sub.2 C.sub.6     H.sub.5 7-COOH CH.sub.3 H H C.sub.6 H.sub.4-o-OH 4 4-CH.sub.2 C.sub.6     H.sub.11 C.sub.3 H.sub.7n 6-COOCH.sub.3 7-CH.sub.2 C.sub.6 H.sub.11     CH.sub.3 H H CH.sub.2 CH.sub.2 OH 4 4-CH.sub.2 CH(OH)CH.sub.2 OH C.sub.3     H.sub.7n 6-CHO 7-CH.sub.2 CH(OH)CH.sub.2 OH CH.sub.3 H H CH.sub.2     CH.sub.2-p-OSO.sub.3 K 4 4-CH.sub.2 CH.sub.2SO.sub.3 K H 6-CONH.sub.2     7-CH.sub.2 CH.sub.2SO.sub.3 K CH.sub.3 H H C.sub.6 H.sub.4-p-OSO.sub.3 K     4 4-CH.sub.2 OC.sub.6 H.sub.5 H 6-CONHCH.sub.3 7-CH.sub.2 OC.sub.6     H.sub.5 CH.sub.3 C.sub.2 H.sub. 5 C.sub.2 H.sub.5 CH.sub.2 OPh 4     4-CH.sub.2 OOCC.sub.6 H.sub.5 H 5-CH.sub.2 Ph 7-CH.sub.2 OOCC.sub.6     H.sub.5 H H H CH.sub.2 SO.sub.2 NHPh 4 5-CH.sub.2      COOCH.sub.3 H 5-CH.sub.2 SO.sub.3 K 7-CH.sub.2 COOCH.sub.3 CH.sub.3     CH.sub.3 CH.sub.3 CH.sub.2 SO.sub.2 NHCH.sub.3 4 4-C.sub.6      H.sub.4-p-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 H 6-CH.sub.2 OSO.sub.3 K     7-C.sub.6 H.sub.4-p-SO.sub.2 N(C.sub.2 H.sub.5).sub.2 CH.sub.3 CH.sub.3     H C.sub.6 H.sub.4-p-SO.sub.2 NHCH.sub.3 4 4-CH.sub.2 CH.sub.2      NHCOOCH.sub.3 H 6-C.sub.6 H.sub.4-p-SO.sub.3 K 7-CH.sub.2 CH.sub.2     NHCOOCH.sub.3CH.sub.3 CH.sub.3 H C.sub.2 COOCH.sub.3 4 4-CH.sub.2     NHCONHCH.sub.3 H 6-CH.sub.2 CH.sub.2 OH 7-CH.sub.2 NHCONHCH.sub.3     CH.sub.3 CH.sub.3 H CH.sub.2 SO.sub.3 N(CH.sub.3).sub.2 6 4-CH.sub.2     CONH.sub.2 H 4-CH.sub.2 Cl 7-CH.sub.2 CONH.sub.2 CH.sub.3 CH.sub.3 H     C.sub.6 H.sub.4 -p-NHCOOCH.sub.3 4 5-CH.sub.2 CONHCH.sub.3 C.sub.4     H.sub.9n 5-C.sub.6 H.sub.4-p-Br 7-CONH.sub.2 H H H CH.sub.2 CH.sub.2     CONH.sub.2 4 4-CH.sub.2 CON(CH.sub.3).sub.2 H H 7-SO.sub.2 NH.sub.2     CH.sub.3 CH.sub.3 CH.sub.3 C.sub.6 H.sub.4-p-CONHCH.sub.3 4 4-CH.sub.2     CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5 H 6-COCH.sub.3 7-SO.sub.2     NHCH.sub.3 CH.sub.3 CH.sub.3 H C.sub.6 H.sub.4-p-SCH.sub.3 4 4-CH.sub.2     SC.sub.2 H.sub.5 H 6-NO.sub.2 7-SO.sub.2 N(C.sub.2 H.sub.5).sub.2     CH.sub.3 CH.sub.3 H CH.sub.2 CH.sub.2 SCH.sub.3 4,5 5-CH.sub.2 SC.sub.6     H.sub.5 H 6-Cl 7-SO.sub.3 C.sub.6      H.sub.5 CH.sub.3 CH.sub.3 H CH.sub.2C.sub.6 H.sub.4-p-SCH.sub.3 6     4-CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 CH.sub.3 4-CN 7-SCH.sub.3 CH.sub.3     CH.sub.3 H CH.sub.2 SO.sub.2 C.sub.2 H.sub.5 6 2,4-di-CH.sub.2 SO.sub.2     C.sub.6 H.sub.5 CH.sub.3 4-NHSO.sub. 2 CH.sub.3 5,7-di-SCN CH.sub.3     CH.sub.3 H CH.sub.2 SO.sub.2 Ph 4 4-C.sub.6 H.sub.3-o,-p-di-CN CH.sub.3     6-CH.sub.3 7-SO.sub.2 C.sub.6 H.sub.5 CH.sub.3 H H C.sub.6      H.sub.4-p-OSO.sub.3 K 4 4-C.sub.6 H.sub.2-o,-m,-p-tri-Cl CH.sub.3     6-OCH.sub.3 5-CHO7-CN CH.sub.3 H H C.sub.6 H.sub.4-p-OSO.sub.3 K 4     2,6-di-OSO.sub.3 Na CH.sub.3 6-Ph 7-CONHC.sub.2 H.sub.5 CH.sub.3 H H     CH.sub.2 (C.sub.8 H.sub.4 O.sub.2 N) 4 H H 6-CH.sub.2 (C.sub.4 H.sub.4     O.sub.2 N) 7-CON(C.sub.2 H.sub.5).sub.2 CH.sub.3 H H C.sub.2 H.sub.5 4 H     H 5-CH.sub.2 (C.sub.4 H.sub.3 O) 7-C.sub.6 H.sub.11 CH.sub.3 H H C.sub.2     H.sub.5 4 5-CH.sub.2 (C.sub.8 H.sub.4 O.sub.2 N) H H 7-SC.sub.6 H.sub.5     CH.sub.3 H H C.sub.2 H.sub.5 4 5-CH.sub.2 (C.sub.4 H.sub.3 O) H H     7-NHSO.sub.2 C.sub.6 H.sub.5 CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5     C.sub.2 H.sub.5 2 4-OSO.sub.3 K H H 7-CH.sub.3 CH.sub.3 CH.sub.3     CH.sub.3 H

                                      TABLE 3                                     __________________________________________________________________________     ##STR7##                                                                     Cinna-                                                                        moyl                                                                          Group                                                                         Posi-                 Substituents                                            tion                                                                              R.sub.1 on D R.sub.5                                                                            on A     R.sub.1 on C  R.sub.3                                                                            R.sub.7                     __________________________________________________________________________    4  H             H    H        H             H    H                           4  4-NO.sub.2    H    5-COCH.sub.3                                                                           6-CH.sub.3    CH.sub.3                                                                           Ph                          4  4-CN          H    5-NO.sub.2                                                                             6-COCH.sub.3  C.sub.2 H.sub.5                                                                    C.sub.6 H.sub.11            4  5-COCH.sub.3  H    6-Cl     6-OCH.sub.3   H    CH.sub.2CHCH.sub.2          4  4-COPh        CH.sub.3                                                                           6-CN     6-SO.sub.3 Na H    CH.sub.2 OOCC.sub.2                                                           H.sub.5                     5  2,4-di-COOH   CH.sub.3                                                                           4-NHSO.sub.2 CH.sub.3                                                                  6-OCH.sub.2 CH.sub.2 SO.sub.4 K                                                             H    C.sub.6 H.sub.4                                                               -p-OOCCH.sub.3              6  4-OOCCH.sub.3 CH.sub.3                                                                           4-CH.sub.3                                                                             6-OCH.sub.2 CH.sub.2 SO.sub.4 K                                                             H    C.sub.6 H.sub.104-CH.sub                                                      .3                          6  4-NHCOCH.sub.3                                                                              CH.sub.3                                                                           4-OCH.sub.3                                                                            6-CH.sub.3    H    CH.sub.2 CH.sub.2                                                             (C.sub.4 H.sub.4                                                              O.sub.2 N)                  4,6                                                                              4-NHCOPh      CH.sub.3                                                                           5-Ph     6-Ph          CH.sub.3                                                                           CH.sub.2 CH.sub.2                                                             NO.sub.2                    4  4-C.sub.2 H.sub.5                                                                           CH.sub.3                                                                           H        6-NO.sub.2    CH.sub.3                                                                           C.sub.6 H.sub.4                                                               -p-NO.sub.2                 6  4-Ph          H    H        6-OCH.sub.3   CH.sub.3                                                                           CH.sub.2 NHOCCH.sub.3       4  4-OSO.sub.3 K H    H        H             H    CH.sub.2 CH.sub.2                                                             SO.sub.3 K                  4  2,5-di-Cl     H    5-SO.sub.3 Na                                                                          6-NHCOCH.sub.3                                                                              C.sub.2 H.sub.5                                                                    CH.sub.2 NHSO.sub.2                                                           CH.sub.3                    4  2-Cl4-SO.sub.2 CH.sub.3                                                                     H    5-SO.sub.3 Na                                                                          6-NHSO.sub.2 CH.sub.3                                                                       CH.sub.3                                                                           C.sub.6 NHSO.sub.2                                                            CH.sub.3                    4  4-NHSO.sub.2 CH.sub.3                                                                       H    6-OCH.sub.2 CH.sub.2 SO.sub.4 K                                                        6-COOCH.sub.3 CH.sub.3                                                                           C.sub.6 H.sub.4                                                               -p-NHSO.sub.2 CH.sub.3      4  4-COOCH.sub.3 H    6-OCH.sub.2 CH.sub.2 SO.sub.4 K                                                        6-COOH        H    C.sub.6 H.sub.104-NHOCCH                                                      .sub.3                      4  2-OCH.sub.3   C.sub.2 H.sub.5                                                                    5-NHCOPh 6-Cl          CH.sub.3                                                                           CH.sub.2 CH.sub.2 Cl        5  4-OC.sub.2 H.sub.5                                                                          C.sub.2 H.sub.5                                                                    4-NHCOPh 5,6-di-Br     C.sub.2 H.sub.5                                                                    C.sub.6 H.sub.4 -p-Br       6  4-SO.sub.3 Na C.sub.2 H.sub.5                                                                    4-NHCOCH.sub.3                                                                         5,6-di-Br     H    C.sub.6 H.sub.4 -p-CN       6  2-SO.sub.3 Na C.sub.2 H.sub.5                                                                    4-OOCC.sub.2 H.sub.5                                                                   5-OCH.sub.36-NHCOCH.sub.3                                                                   H    CH.sub.2 CH.sub.2 CN        4  2-OCH.sub.34-SO.sub.3 K                                                                     H    5-COOH   6-CH.sub.2 OOCCH.sub.3                                                                      H    CH.sub.2 CH.sub.2                                                             OC.sub.2 H.sub.5            6  4-OCH.sub.2 CH.sub.2 OSO.sub.3 K                                                            H    H        6-CH.sub.2 Cl H    CH.sub.2 CH.sub.2                                                             OCH.sub.2 CH.sub.2                                                            OC.sub.2 H.sub.5            4,6                                                                              2-SO.sub.3 Na5-Cl                                                                           H    H        6-CN          H    CH.sub.2 Ph                 6  4-Cl          H    4-SO.sub.2 CH.sub.3                                                                    6-OOCCH.sub.3 CH.sub.3                                                                           CH.sub.2 C.sub. 6                                                             H.sub.11                    4  4-OH          H    6-CF.sub.3                                                                             5-COOH        CH.sub.3                                                                           C.sub.6 H.sub.4 -o-OH       4  4-CH.sub.2 OOCCH.sub.3                                                                      C.sub.3 H.sub.7n                                                                   6-COOCH.sub.3                                                                          5-OH          CH.sub.3                                                                           CH.sub.2 CH.sub.2 OH        4  4-SO.sub.3 K  C.sub.3 H.sub.7n                                                                   6-CHO    5-CH.sub.2 CHCH.sub.2                                                                       C.sub.2 H.sub.5                                                                    CH.sub.2 CH.sub.2SO.sub.                                                      3 K                         4  4-OPh         H    6-CONH.sub.2                                                                           6-CH.sub.3    CH.sub.3                                                                           C.sub.6 H.sub.4                                                               -p-OSO.sub.3 K              4  4-NO.sub.2    H    6-CONHCH.sub.3                                                                         6-COCH.sub.3  CH.sub.3                                                                           CH.sub.2 OPh                4  5-CN          H    6-CH.sub.2 Ph                                                                          6-OCH.sub.3   H    CH.sub.2 SO.sub.2 NHPh      4  4-COCH.sub.3  H    6-CH.sub.2 SO.sub.3 K                                                                  6-SO.sub.3 Na CH.sub.3                                                                           CH.sub.2 SO.sub.2                                                             NHCH.sub.3                  4  5-CH.sub.3    H    6-CH.sub.2 OSO.sub.3 K                                                                 6-OCH.sub.2 CH.sub.2 SO.sub.4 K                                                             H    C.sub.6 H.sub.4                                                               -p-SO.sub.2 NHCH.sub.3      4  5-Ph          H    5-C.sub.6 H.sub.4 -p-SO.sub.3 K                                                        6-OCH.sub.2 CH.sub.2 SO.sub.3 K                                                             H    CH.sub.2 COOCH.sub.3        4  5-OCH.sub.3   H    5-CH.sub.2 CH.sub.2 OH                                                                 6-CH.sub.3    H    CH.sub.2 SO.sub.2                                                             N(CH.sub.3).sub.2           4  4,5-di-Br     H    5-CH.sub.2 Cl                                                                          6-Ph          H    C.sub.6 H.sub.4                                                               -p-NHCOOCH.sub.3            4  5-COOH        C.sub.4 H.sub.9n                                                                   6-C.sub.6 H.sub.4 -p-Br                                                                6-NO.sub.2    C.sub.2 H.sub.5                                                                    CH.sub.2 CH.sub.2                                                             CONH.sub.2                  4  H             H    H        6-OCH.sub.3   C.sub.2 H.sub.5                                                                    C.sub.6 H.sub.4                                                               -p--CONHCH.sub.3            4  4-NO.sub.2    H    6-COCH.sub.3                                                                           6-NHCOCH.sub.3                                                                              CH.sub.3                                                                           C.sub.6 H.sub.4                                                               -p-SCH.sub.3                4  4-CN          H    6-NO.sub.2                                                                             6-NHSO.sub.2 CH.sub.3                                                                       C.sub.3 H.sub.7n                                                                   CH.sub.2 CH.sub.2                                                             SCH.sub.3                   4  5-COCH.sub.3  H    6-Cl     6-COOCH.sub.3 H    CH.sub.2C.sub.6 H.sub.4                                                       -p-SCH.sub.3                4  4-COPh        CH.sub.3                                                                           5-CN     6-COOH        CH.sub.3                                                                           CH.sub.2 SO.sub.2                                                             C.sub.2 H.sub.5             4  2,4-di-COOH   CH.sub.3                                                                           5-NHSO.sub.2 CH.sub.3                                                                  8-Cl          H    CH.sub.2 SO.sub.2 Ph        4  4-OOCCH.sub.3 CH.sub.3                                                                           5-CH.sub.3                                                                             5,6-di-Br     H    CH.sub.2 CH.sub.2                                                             OSO.sub.3 K                 4  4-NHCOCH.sub.3                                                                              CH.sub.3                                                                           5-OCH.sub.3                                                                            5,6-Di-Br     H    C.sub.6 H.sub.4                                                               - p-OSO.sub.3 K             4  4-NHCOPh      CH.sub.3                                                                           6-Ph     5-OCH.sub.36-NHCOCH.sub.3                                                                   H    CH.sub.2 (C.sub.8                                                             H.sub.4 O.sub.2 N)          5  4-CH.sub.2 CHCH.sub.2                                                                       H    H        6-NHCOCH.sub.3                                                                              C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5             4,6                                                                              H             CH.sub.3                                                                           H        6-OCPh        C.sub.2 H.sub.5                                                                    C.sub.2 H.sub.5             6  4-CONH.sub.2  H    H        6-CH.sub.2 CONHCH.sub.3                                                                     H    H                           6  3-SO.sub.2 NH.sub.2                                                                         H    4-COCH.sub.3                                                                           6-CH.sub.2 CON(CH.sub.3).sub.2                                                              CH.sub.3                                                                           Ph                          4  4-SO.sub.2 NHCH.sub.3                                                                       H    5-NO.sub.2                                                                             6-CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2                                        OC.sub.2 H.sub.5                                                                            C.sub.2 H.sub.5                                                                    C.sub.6 H.sub.11            4  4-SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                         H    6-Cl     6-CH.sub.2 SC.sub.2 H.sub.5                                                                 H    CHCHCH.sub.2                4  4-SO.sub.3 C.sub.6 H.sub.5                                                                  CH.sub.3                                                                           6-CN     6-CH.sub.2 SC.sub.6 H.sub.5                                                                 H    CH.sub.2 OOCC.sub.2                                                           H.sub.5                     5  4-SCH.sub.3   CH.sub.3                                                                           4-NHSO.sub.2 CH.sub.3                                                                  6-CH.sub.2 SO.sub.2 C.sub.2 H.sub.5                                                         H    C.sub.6 H.sub.10                                                              -p-OOCCH.sub.3              6  2,4-di-SCN    CH.sub.3                                                                           4-CH.sub.3                                                                             6-CH.sub.2 SO.sub.2 C.sub.6 H.sub.5                                                         H    C.sub.                                                                        6 H.sub.104-CH.sub.3        4  4-SO.sub.2 C.sub.6 H.sub.5                                                                  CH.sub.3                                                                           6-OCH.sub.3                                                                            6-C.sub.6 H.sub.3 -o, -p-di-CN                                                              H    CH.sub.2 CH.sub.2(C.sub.                                                      4 H.sub.4 O.sub.2 N)        4  2-CHO4-CN     CH.sub.3                                                                           6-Ph     6-C.sub.6 H.sub.2 -o,m,p-tri-Cl                                                             CH.sub.3                                                                           CH.sub.2 CH.sub.2                                                             NO.sub.2                    4  4-CONHC.sub.2 H.sub.5                                                                       CH.sub.3                                                                           H        6,8-di-OSO.sub.3 NH(CH.sub.3).sub.3                                                         CH.sub.3                                                                           C.sub.6 H.sub.4                                                               -p-NO.sub.2                 4  4-CON(C.sub.2 H.sub.5).sub.2                                                                H    H        5,6-di-OSO.sub.3 Na                                                                         CH.sub.3                                                                           CH.sub.2 NHOCCH.sub.3       4  3-C.sub.6 H.sub.11                                                                          H    5,6-di-SO.sub.3 Na                                                                     5,6-di-OSO.sub.3 Na                                                                         C.sub.2 H.sub.5                                                                    CH.sub.2 NHSO.sub.2                                                           CH.sub.3                    4  3-SC.sub.6 H.sub.5                                                                          H    6-SO.sub.3 Na                                                                          5,6-di-SO.sub.3 NH(CH.sub.3).sub.3                                                          CH.sub.3                                                                           C.sub.6 H.sub.4                                                               -p-NHOCCH.sub.3             4  3-SC.sub.6 H.sub.5                                                                          H    6-SO.sub.3 Na                                                                          5,6-di-SO.sub.3 NH(CH.sub.3).sub.3                                                          CH.sub.3                                                                           C.sub.6 H.sub.4                                                               -p-NHOCCH.sub.3             4  4-NHSO.sub.2 C.sub.6 H.sub.5                                                                H    6-OCH.sub.2 CH.sub.2 SO.sub.4 K                                                        5,6-di-OSO.sub. 3 Na                                                                        CH.sub.3                                                                           C.sub.6 H.sub.4                                                               -p-NHSO.sub.2 CH.sub.3      4  4-SC.sub.6 H.sub.11                                                                         H    5-OCH.sub.2 CH.sub.2 SO.sub.4 K                                                        6-SC.sub.6 H.sub.11                                                                         H    C.sub.6 H.sub.104-NHOCCH                                                      .sub.3                      4  4-C.sub.6 H.sub.4 -p-CH.sub.3                                                               C.sub.2 H.sub.5                                                                    6-NHCOPh 6-C.sub.6 H.sub.4 -p-CH.sub.3                                                               CH.sub.3                                                                           CH.sub.2 CH.sub.3 Cl        5  4-C.sub.6 H.sub.4 -p-CH.sub.2 CHCH.sub.2                                                    C.sub.2 H.sub.5                                                                    4-NHCOPh 6-C.sub.6 H.sub.4 -p-CH.sub.2 CHCH.sub.2                                                    C.sub.2 H.sub.5                                                                    C.sub.6 H.sub.4 -p-Br       6  4-OCH.sub.2 CH.sub.2 NO.sub.2                                                               C.sub.2 H.sub.5                                                                    4-NHCOCH.sub.3                                                                         6-OCH.sub.2 CH.sub.2 NO.sub.2                                                               H    C.sub.6 H.sub.4 -p-CN       4  2-CH.sub.2 NHCOCH.sub.3                                                                     C.sub.2 H.sub.5                                                                    6-OOCC.sub.2 H.sub.5                                                                   6-CH.sub.2 NHCOCH.sub.3                                                                     H    CH.sub.2 CH.sub.2 CN        4  4-CH.sub.2 NHSO.sub.2 C.sub.2 H.sub.5                                                       H    6-COOH   6-CH.sub.2 NHSO.sub.2 C.sub.2 H.sub.5                                                       H    CH.sub.2 CH.sub.2                                                             OC.sub.2 H.sub.5            4  4-CH.sub.2 CH.sub.2 Cl                                                                      H    H        6-CH.sub.2 CH.sub.2 Cl                                                                      H    CH.sub.2 CH.sub.2                                                             OCH.sub.2 CH.sub.2                                                            OC.sub.2 H.sub.5            4,6                                                                              2,6-di-CH.sub.2 CN                                                                          H    H        5,6-di-CH.sub.2 CN                                                                          H    CH.sub.2 Ph                 6  4-CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                        H    4-SO.sub.2 CH.sub.3                                                                    6-CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                        CH.sub.3                                                                           CH.sub.2 C.sub.6                                                              H.sub.11                    6  4-CH.sub.2 C.sub.6 H.sub.5                                                                  H    4-CH.sub.2 C.sub.6 H.sub.5                                                             6-COOH        CH.sub.3                                                                           C.sub.6 H.sub.4 -o-OH       4  4-CH.sub.2 C.sub.6 H.sub.11                                                                 C.sub.3 H.sub.7n                                                                   6-COOCH.sub.3                                                                          6-CH.sub.2 C.sub.6 H.sub.11                                                                 CH.sub.3                                                                           CH.sub.2 CH.sub.2 OH        4  4-CH.sub.2 CH(OH)CH.sub.2 OH                                                                C.sub.3 H.sub.7n                                                                   6-CHO    6-CH.sub.2 CH(OH)CH.sub.2 OH                                                                C.sub.2 H.sub.5                                                                    CH.sub.2 CH.sub.2SO.sub.                                                      3 K                         4  4-CH.sub.2 CH.sub.2SO.sub.3 K                                                               H    5-CONH.sub.2                                                                           6-CH.sub.2 CH.sub.2SO.sub.3 K                                                               CH.sub.3                                                                           C.sub.6 H.sub.4                                                               -p-OSO.sub.3 K              4  4-CH.sub.2 OC.sub.6 H.sub.5                                                                 H    5-CONHCH.sub.3                                                                         6-CH.sub.2 OC.sub.6 H.sub.5                                                                 CH.sub.3                                                                           CH.sub.2 OPh                4  4-CH.sub.2 OOCC.sub.6 H.sub.5                                                               H    5-CH.sub.2 Ph                                                                          6-CH.sub.2 OOCC.sub.6 H.sub.5                                                               H    CH.sub.2 SO.sub.2 NHPh      4  5-CH.sub.2 COOCH.sub.3                                                                      H    6-CH.sub.2 SO.sub.3 K                                                                  5-CH.sub.2 COOCH.sub.3                                                                      CH.sub.3                                                                           CH.sub.2 SO.sub.2                                                             NHCH.sub.3                  4  4-C.sub.6 H.sub.4 -p-SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                      H    6-CH.sub.2 OSO.sub.3 K                                                                 6-C.sub.6 H.sub.4 -p-SO.sub.2 N(C.sub.2                                       H.sub.5).sub.2                                                                              H    C.sub.6 H.sub.4                                                               -p-SO.sub.2 NHCH.sub.3      4  4-CH.sub.2 CH.sub.2 NHCOOCH.sub.3                                                           H    6-C.sub.6 H.sub.4 -p-SO.sub.3 K                                                        6-CH.sub.2 CH.sub.2 NHCOOCH.sub.3                                                           H    CH.sub.2 COOCH.sub.3        4  4-CH.sub.2 NHCONHCH.sub.3                                                                   H    6-CH.sub.2 CH.sub.2 OH                                                                 6-CH.sub.2 NHCONHCH.sub.3                                                                   H    CH.sub.2 SO.sub.2                                                             N(CH.sub.3).sub.2           4  4-CH.sub.2 CONH.sub.2                                                                       H    6-CH.sub.2 Cl                                                                          6-CH.sub.2 CONH.sub.2                                                                       H    C.sub.6 H.sub.4                                                               -p-NHCOOCH.sub.3            4  5-CH.sub.2 CONHCH.sub.3                                                                     C.sub.4 H.sub.9n                                                                   6-C.sub.6 H.sub.4 -p-Br                                                                6-CONH.sub.2  C.sub. 2 H.sub.5                                                                   CH.sub.2 CH.sub.2                                                             CONH.sub.2                  4  4-CH.sub.2 CON(CH.sub.3).sub.2                                                              H    H        6-SO.sub.2 NH.sub.2                                                                         C.sub.2 H.sub.5                                                                    C.sub.6 H.sub.4                                                               -p-CONHCH.sub.3             4  4-CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                     H    5-COCH.sub.3                                                                           6-SO.sub.2 NHCH.sub.3                                                                       CH.sub.3                                                                           C.sub.6 H.sub.4                                                               -p-SCH.sub.3                4  4-CH.sub.2 SC.sub.2 H.sub.5                                                                 H    5-NO.sub.2                                                                             6-SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                         C.sub.3 H.sub.7n                                                                   C.sub.2 CH.sub.2                                                              SCH.sub.3                   4  5-CH.sub.2 SC.sub.6 H.sub.5                                                                 H    5-Cl     6-SO.sub.3 C.sub.6 H.sub.5                                                                  H    CH.sub.2C.sub.6 H.sub.4                                                       -p-SCH.sub.3                4  4-CH.sub.2 SO.sub.2 C.sub.2 H.sub.5                                                         CH.sub.3                                                                           5-CN     6-SCH.sub.3   CH.sub.3                                                                           CH.sub.2 SO.sub.2                                                             C.sub.2 H.sub.5             4,5                                                                              2,4-di-CH.sub.2 SO.sub.2 C.sub.6 H.sub.5                                                    CH.sub.3                                                                           6-NHSO.sub.2 CH.sub.3                                                                  5,6-di-SCN    H    CH.sub.2 SO.sub.2 Ph        6  4-C.sub.6 H.sub.3 -o, -p-di-CN                                                              CH.sub.3                                                                           4-CH.sub.3                                                                             6-SO.sub.2 C.sub.6 H.sub.5                                                                  H    CH.sub.2 CH.sub.2                                                             OSO.sub.3 K                 4  4-C.sub.6 H.sub.2 -o, -m, -p-tri-Cl                                                         CH.sub.3                                                                           5-OCH.sub.3                                                                            5-CHO-6-CN    H    C.sub.6 H.sub.4(C.sub.8                                                       H.sub.4 O.sub.2 N)          4  H             H    6-CH.sub.2 (C.sub.4 H.sub.4 O.sub.2 N)                                                 6-CON(C.sub.2 H.sub.5).sub.2                                                                H    C.sub.2 H.sub.5             4  H             H    6-CH.sub.2 (C.sub.4 H.sub.3 O)                                                         6-C.sub.6 H.sub.11                                                                          H    C.sub.2 H.sub.5             4  5-CH.sub.2 (C.sub.8 H.sub.4 O.sub.2 N)                                                      H    H        6-SC.sub.6 H.sub.5                                                                          H    C.sub.2 H.sub.5             4  5-CH.sub.2 (C.sub.4 H.sub.3 O)                                                              H    H        6-NHSO.sub.2 C.sub.6 H.sub.5                                                                H    C.sub.2 H.sub.5             __________________________________________________________________________

The invention has been described in detail with particular reference topreferred embodiments thereof, but it will be understood that variationsand modifications can be effected within the spirit and scope of theinvention.

I claim:
 1. A dye having the structure: ##STR8## wherein the A ring isunsubstituted or substituted in any positions not occupied by cinnamoylgroups; R₅ is H or alkyl; and each R₁ and each A ring substituent isselected from alkyl, alkenyl or 2-6 carbon atoms, aryl, cyclohexyl,alkoxy, halogen, hydroxy, alkylsulfonyl, cyano, carbamoyl, alkanoyl,alkanoyloxy, aroyl, alkoxycarbonyl, sulfamoyl, alkylsulfamoyl,dialkylsulfamoyl, alkanoylamino, SO₃ C₆ H₅, amino, alkylthio, thiocyano,arylsulfonyl, formyl, alkylcarbamoyl, dialkylcarbamoyl, NO₂, --SO₃ M,--OSO₃ M, --COOH, aryloxy, arylthio, alkylsulfonylamino, aroylamino,arylsulfonylamino, and cyclohexylthio, wherein each of the alkyl,alkenyl, aryl, and cyclohexyl moieties of the above groups, isunsubstituted or substituted with 1-3 substituents different from thesaid moiety and independently selected from alkanoyloxy, alkyl, alkenyl,succinimido, --NO₂, alkanoylamino, alkylsulfonylamino,1-(2-pyrrolidono), halogen, cyano, alkoxy, aryl, cyclohexyl, hydroxy,--SO₃ M, --OSO₃ M, aryloxy, furyl, aroyloxy, alkoxycarbonyl, --SO₂N-(alkyl)₂, --NHCOO-alkyl, --NHCONH-alkyl, glutarimido, phthalimido,CONH₂, CONH-alkyl, CON(alkyl)₂, alkoxyalkoxy, alkylthio, arylthio,alkylsulfonyl, and arylsulfonyl, wherein M is selected from H⁺, NH₄ ⁺,Na⁺, K⁺, and the colorless cations of sulfuric or sulfonic acid salts oftrimethylamine, triethylamine, tri(2-hydroxyethyl)amine,di(2-hydroxyethyl)amine, or N,N-dimethylaniline; and the coupler C¹ isselected from ##STR9## wherein each R₁ is as defined above; R₂ and R₇are each selected independently from hydrogen, alkyl, alkenyl of 2-6carbon atoms, aryl, and cyclohexyl, all of which groups areunsubstituted or substituted as defined above for the substituted R₁groups; and R₃, R₄ and R₈ are each selected from hydrogen and alkyl. 2.A dye of claim 1 wherein the coupler C¹ is ##STR10## wherein R₁, R₂, andR₇ are as defined therein.
 3. A dye of claim 1 wherein the coupler C¹ is##STR11## wherein R₁, R₃, R₄, R₇, and R₈ are as defined therein.
 4. Adye of claim 1 wherein the coupler C¹ is ##STR12## wherein R₁, R₃, andR₇ are as defined therein.
 5. A dye according to claim 1 wherein: the Aring is unsubstituted or substituted with 1-3 substituents independentlyselected from methoxycarbonyl, β-hydroxyethylcarbamoyl, CF₃, NO₂,alkanoyl, alkylsulfonyl, alkoxy, β-potassiosulfatoethylcarbamoyl,halogen, CN, methylcarbamoyl, carbamoyl, ethoxycarbonyl, and methyl; thecinnamoyl ring is unsubstituted or substituted with 1-3 substituentsindependently selected from alkyl, aralkyl, aralkyl substituted with--SO₃ M or --SO₄ M, cyclohexylalkyl, cyclohexylalkyl substituted with--SO₃ M or --SO₄ M, alkoxy, and alkanoylamino; R₂ is H, alkyl, aralkyl,alkyl or aralkyl substituted with --SO₃ M or --SO₄ M, cyclohexylalkyl,cyclohexylalkyl substituted with --SO₃ M or --SO₄ M; R₇ is H, alkyl,aralkyl, aralkyl substituted with --SO₃ M or --SO₄ M, cyclohexylalkyl,cyclohexylalkyl substituted with --SO₃ M or --SO₄ M, sodio- orpotassiosulfatoalkyl, sodio- or potassiosulfonicalkyl, oralkanoyloxyalkyl; the couplers are unsubstituted or substituted with 1-3substituents independently selected from aralkyl, aralkyl substitutedwith --SO₃ M or --SO₄ M, cyclohexylalkyl, cyclohexylalkyl substitutedwith --SO₃ M or --SO₄ M, --SO₃ Na, --SO₃ K, --SO₃ N⁺ H(CH₃)₃, halogen,--SO₄ Na, --SO₄ K, --SO₄ N⁺ H(CH₃)₃, alkyl, alkoxy, --COOH, and --OH;R₃, R₄ and R₈ are H or alkyl; and R₅ is hydrogen.
 6. A dye according toclaim 1 wherein: the cinnamoyl ring is unsubstituted or substituted withhalogen, COOH, OH, or SO₃ M; ring A is unsubstituted or substituted withalkyl, halogen, CN, alkoxy, COOalkyl, CONH₂ ; alkanoylamino,CONHalkylene--SO₄ M, hydroxyethylcarbamoyl, or CONHalkyl; and wherein,in an aniline coupler each substituent R₁ is a methyl, methoxy oracetamido group or a chlorine atom, each R₂ is hydrogen, a methyl orethyl group, or a sulfonated cyclohexyl or benzyl group and each R₇ anethyl or sulfonated ethyl group or an alkyl group of up to 4 carbonatoms substituted with a sulfonated phenyl group, each sulfonate groupbeing of formula --SO₃ M, and wherein in a tetrahydroquinoline couplerR¹ and R³ are methyl groups, each of R₄ and R₈ is hydrogen or a methylgroup, and R₇ is an ethyl group or a group of formula CH₂ CH₂ OCOCH₃ orCH₂ CH₂ OSO₃ M.
 7. A dye according to claim 1 wherein the coupler C¹ isselected from those of the formula ##STR13## wherein R₂ is alkyl, R₇ isH, alkyl or alkyl substituted with OSO₃ M or SO₃ M, and the phenyl ringis substituted with 1 or 2 groups independently selected from alkyl,alkoxy and alkanoylamino.
 8. A dye according to claim 1 wherein ring Ais unsubstituted or substituted with 1 or 2 substituents independentlyselected from cyano, halogen, alkyl, alkoxy and acylamido.
 9. A dyeaccording to claim 1 having the formula ##STR14##
 10. A dye according toclaim 1 having the formula ##STR15##
 11. A dye according to claim 1having the formula ##STR16##